2-(furan-2-yl)-10-thia-5,7,12-triazatetracyclo[11.7.0.0^{3,11}.0^{4,9}]icosa-1(13),2,4(9),5,7,11-hexaen-8-amine

ID: ALA1091450

PubChem CID: 46884360

Max Phase: Preclinical

Molecular Formula: C20H20N4OS

Molecular Weight: 364.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1sc1nc3c(c(-c4ccco4)c12)CCCCCCC3

Standard InChI:  InChI=1S/C20H20N4OS/c21-19-18-17(22-11-23-19)16-15(14-9-6-10-25-14)12-7-4-2-1-3-5-8-13(12)24-20(16)26-18/h6,9-11H,1-5,7-8H2,(H2,21,22,23)

Standard InChI Key:  WMISFEODCMGWDV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 30  0  0  0  0  0  0  0  0999 V2000
    7.5813   -1.6081    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5835    0.0431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2971   -0.3673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2946   -1.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0849   -1.4587    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.0891   -0.1128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5722   -0.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3966   -0.7064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7389    0.0498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2506    0.7253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4280    0.6403    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8774   -1.3768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5805    0.8643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2477    1.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9923    2.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1672    2.1336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9128    1.3488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3411   -1.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5262   -1.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8200   -1.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8683   -1.1940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8678   -0.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3434    0.2630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5340    0.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5426   -0.7789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8272   -0.0055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  8 12  1  0
 13 14  2  0
  5  7  1  0
  6  3  1  0
  3  2  2  0
  2 22  1  0
  6  7  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 13  1  0
  2 13  1  0
  3  4  1  0
  7  8  1  0
 21  1  1  0
  8  9  2  0
  1  4  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 25 20  1  0
 25 26  1  0
 26 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1091450

   2-(Furan-2-yl)-10-thia-5,7,12-triazatetracyclo[11.7.0.03,11.04,9]icosa-1(13),2,4(9),5,7,11-hexaen-8-amine

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 364.47

Molecular Weight (Monoisotopic): 364.1358

AlogP: 5.13

#Rotatable Bonds: 1

Polar Surface Area: 77.83

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 2.64

CX LogP: 4.69

CX LogD: 4.69

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.51

Np Likeness Score: -1.35

References

1. Lockman JW, Reeder MD, Suzuki K, Ostanin K, Hoff R, Bhoite L, Austin H, Baichwal V, Adam Willardsen J..  (2010)  Inhibition of eEF2-K by thieno[2,3-b]pyridine analogues.,  20  (7): [PMID:20189382] [10.1016/j.bmcl.2010.02.005]

Source

Source(1):

• Scientific Literature